What were Chiang Kai-shek's biggest strategic blunders during the Second Sino-Japanese war?

The nationalist Chinese were in a completely untenable position in World War II. They were facing a foreign enemy whom they had no hope of defeating, and an internal rebellion. That Chiang Kai-Shek was able to simply stay in power and maintain a cohesive government is testament to his ability. The "war" with Japan was more of an organized retreat than any kind of battle. Sure, he could have simply abandoned Shanghai and lost fewer men, but considering that it was his capital and the home of all of his supporters, that would not have been possible politically.

On what basis is it correct to assert Chiang Kaishek's actions were strategic blunders?

Instead of cycling through the endless characterisation of his actions, let's stick to one, the Battle of Shanghai (August 13, 1937 – November 26, 1937) (note: the dates are important, so let's keep it in mind).

At this battle, Chiang Kaishek sent his best 2 divisions, the 87th and the 88th (& residuals of Fengtian Army). He persisted for 3 months against overwhelming odds of about 10 divisions of Japanese Army (better equipped, trained, fed and more mobile). The best estimate of Japanese losses is 9,115 killed and 31,257 wounded, while Chinese casualties reached a staggering 187,000.

What is normally never mentioned is the reason for this staggering difference. His soldiers were dying by the day at huge differentials, but he was in fact waiting for support and help from the international community -- which never came. Why? There were busy convening a meeting in Brussels, beginning late October 1937 - Nine Power Treaty Conference. Here's the relevant parts from Wikipedia (earlier link):

On November 24, the Nine-Power Treaty Conference convened for the last time and then adjourned indefinitely, without producing any measures that would stop Japanese aggression. At this point, the Washington System had completely collapsed.

In his report, General Chen Cheng wrote that throughout much of the Shanghai campaign, sound military strategy was often supplanted by political strategy. It was the nation's tragedy that political strategy, especially the one as precarious as the hope for foreign intervention, forced the troops to make exorbitant sacrifices in Shanghai and led almost to total annihilation. He wrote that because China was weak, it was in dire need of foreign help and had to sacrifice just to prove its capacity to fight and will to resist. By the end of the battle, even though hundreds of thousands of Chinese troops died just to make the point that China was ready to sacrifice, the final hope for a western intervention never materialized.

Strategic blunder? Yes. By whom, is the real question? I think it a tail wagging the dog hiding from having to make principled decisions. The international community lost a friend who needed help then, back in 1937. To this day, some still remember -- in Taiwan and China.

Mao and his successors learnt this lesson well. Hence, the Korean War which gave rise to the Cold war.

I find that this question should be refused since every answer is inevitably going to be an opinion (and exchanging opinions is presumably not the goal of history stackexchange).

That being said, I will voice a rebellious and dissonant opinion about what could be Chiang's greatest blunder (purely in military terms):

A conventional approach to improve China's military situation in 1937-1945 seems hopeless no matter what: training, weaponry, experience of the Chinese army is universally inferior to the Japanese army and curruption knows no bounds within the Chinese ranks. China has (initially) no strong allies to rely on. At the same time, China is fighting at home and has a huge potential reserve of manpower. Hence my verdict: Chiang's greatest blunder is his lack of revolutionary zeal and his failure/refusal to turn the Chinese-Japanese war into a revolutionary war (not necessarily Communist revolution, it could e.g. be seen as a continuation as the Xinhai "bourgeois" revolution and its values, ideas and goals).

Remember the wreck that France was in in 1792: Many of the able French troops and officers were royalists who had deserted. Robespierre however appealed to the large French masses and urged them to take up arms while crushing internal strife and removing corrupt officials through the reign of terror. This, together with the new military practice of "promotion by merit", led to a string of succesful military pushbacks against the combined Prussian and Austrian armies and the eventual conquest of the Southern low countries. In later years, Robespierre's reforms would yield even greater military dividends.

Also remember Mao's victory -against all odds- over the KMT during 1945-1949: while Chiang had to spend all the time keeping his warlord-clique loyal to his administration, the communist generals coordinated the PLA as one military body (often after arguing ad nauseam about the tactics to choose), a military body that had no difficulty in recruiting new troops either from the peasantry -who were in it for the promised land reforms- or from defecting nationalist troops -whose officers would e.g. often-time betray their troops by selling the army's food and resources in order to fill their own pockets-.

Chiang was a figure unable to transcend the sclerotic and corrupt mess that was warlord-China during a time that China needed a Robespierre to do just that. China held all the cards to conduct successful revolutionary war against the Japanese at that time (perhaps relying more on guerilla-tactics compared with the French case, because of the greater technological disadvantage China had compared to Japan than France had compared to GB/Austria/Prussia).

Picking the biggest blunder for Chiang is hard because ultimately, for WWII, the Chinese theatre was not decisive. The war was decided by naval battles in the Pacific, and to a lesser extent, the late entry of USSR. But his actions did have a big impact on the post-WWII Chinese Civil War, and by extension the Cold War. This is similar to how the Western Front played a lesser role in the victory over Nazi Germany, but it had a huge effect on post-war Europe.

In this light, the episode that had the biggest post-war impact, both to Chiang and China, was Operation Ichi-Go. In this massive land operation (Japan's largest ever), the Imperial Japanese Army succeeded in neutralising airbases being used to bomb the home islands, and established a land route to Indochina. But this was strategically pointless as the naval war had worsened to the point where the US can bomb Japan from the Mariana islands. Chiang's Nationalist regime was also a loser, having lost massive amounts of territory and men. In fact the only winner was the Communists, who established themselves in the vacuum of North China left by Japan.

To be fair, the scale of the attack was unprecedented, and the outcome may not have been much different even if the Nationalists made fewer mistakes. But the worst effect was that Chiang and the Nationalists' perceived incompetence contributed to the loss of confidence the US had in them, which led to the withdrawal of support during the civil war, and the loss of China. Here Chiang shares the blame with his lieutenants, as well as the poor handling by Stilwell and Roosevelt.

Exactly how bad this loss of prestige could be seen in two events:

• in 1943, where at the Cairo Conference, a beaming Chiang and a scowling Churchill flank Roosevelt; Chiang at the apex of his prestige, with the full support of Roosevelt, who believed a victorious China would become the foremost Asian power to lead its post-war revival, and conversely the British Empire's influence would wane.
• then in 1945, where at the Potsdam Conference, despite producing the Potsdam Declaration, Chiang was not even in attendance.

Where could Chiang have done better? Let's look at a timeline:

13 Apr-25 May 1944 (Battle of Henan): Japanese attack and connect Beijing and Wuhan, by attacking from both North and South.

• Chinese defenders' performance was unremarkable, especially given their commander Tang Enbo was considered one of their best. This war area had gone many years without major battles, which was a big factor in their unpreparedness.
• Chinese intelligence had plenty of forewarning about this attack, but it was not acted upon.

Jun-Aug 1944 Battle of Changsha (1944): Japanese attack and quickly take Changsha. Pushing further, they were held at Hengyang for a long period, taking it eventually after 47 days.

• The preparation for this battle was woefully inadequate. Its scale could have been foreseen given the earlier battle and intelligence on troop buildup around Wuhan.
• The Chinese were tactically trumped; Xue Yue chose to use the same tactics he used in previous battles, by luring the enemy deep into a strong point (Changsha) then encircling them. But Isamu Yokoyama adapted to exactly counter these tactics, by placing his strongest forces on the flanks, ignoring attacks designed to lure, and destroying strong points before the Chinese could react and regroup.
• After the fall of Changsha, Chiang wanted the city of Hengyang to be held at all costs, while forces regrouped and performed an encirclement there. This proved to be too optimistic; while the defenders held a record 47 days at Hengyang, the other Chinese forces could not successfully regroup and relieve them.

16 August - 24 November 1944 Battle of Guilin–Liuzhou: Japanese continue their attack and take Guilin/Liuzhou by attacking from two directions: from Hengyang in the North, and from Canton in the Southeast.

• By this stage Chiang was rapidly losing the US's trust. He began pulling troops from Burma which made this worse. Joseph Stilwell used this opportunity to attempt to remove Chiang from power; this failed and Stilwell was replaced instead, but the PR damage was irreparable.
• Due to being spent at Hengyang, the Chinese could not mount an effective defense, and many positions were lost without a fight. Bai Chongxi was sent to command the defense but could do little to avert disaster.

As supreme commander, Chiang was more or less responsible for all of these. Chief among the errors were:

• Severely underestimating Japan and her ability to undertake such a large scale operation this late into the war. Chiang became complacent and assumed victory was just a matter of time and there would be no hiccups.

  Chiang persistently underestimated the Japanese ability to launch attacks on a scale larger than the 1941 campaigns against either Changsha or Changde, which his armies had resisted until the Japanese were forced to withdraw

• Ignoring intelligence pointing to massive troop movements and concentrations during the leadup to the battles. Although better preparations may not have affected the outcome of the battles much, given the unprecedented scale of the attacks, acting upon and sharing this intelligence with the US would have greatly mitigated the damage to his reputation.

  While Chiang’s intelligence people are hardly free from blame, his temperament and misjudgements also played a role in undermining Nationalist military campaigns.

• Being overly optimistic and planning defenses that were wildly unrealistic. Changsha could not be held, and certainly not by using the exact same tactics as last time - although Xue Yue takes most of the blame here, Chiang was one of a few people in China who could have overruled him. A defense at Hengyang from the start would have been much more successful. Alternately, given the loss of Changsha, instead of holding Hengyang to the death, regrouping at Guilin/Liuzhou would also have been preferable to what happened.

  Once the Japanese launched their unprecedented scale of attacks, Chiang had no strategic alternative other than holding a city, weakening the attacking forces, and mobilizing a much larger force to hopefully inflict a crushing blow on the Japanese forces. Unfortunately, this strategy backfired on three accounts. First, the Japanese army often placed higher priority on the attacking peripheral forces in order to isolate the chosen city. Second, the Japanese placed higher priority to the interception and annihilation of the Chinese reinforcements than the occupation of important cities. Third, the Chinese defenders with the exception of the Fang Xianjue’s 10th Army barely lived up to Chiang Kai-shek’s expectations.

See: Chiang Kai-shek and the Japanese Ichigo Offensive, 1944 by Yung-Fa Chen

China was not just a winner of WWII. It won bigly, getting virtually all the lost territories restored, a permanent seat in the security council, and eventually nuclear power.

So on a strategic level, it is reasonable to say Chiang Kai-shek did at least OK (with what he had).

But with 20/20 historical hindsight, Chiang Kai-shek's clearest mistake was not finishing the civil war with the communist as he had intended.

Turned out he was correct. Japan would eventually be defeated. Japan was but a flesh wound, communism was the cancer.

Many historians claim that Chiang Kai-shek had no hope of winning WWII. But the same could have been said of England, France, or Russia. None of them could have defeated the Axis alone. So what makes China so different? Why do the historians and history buffs sagely tell teach other China could not defeat the Axis?

Of course that was true. But the Axis powers DID declare war on most of the world.

And no nation that fought the Axis had to fight alone. And nobody did.

The Axis bit off more than they could chew. And they choked on their ambition and arrogance.

So regarding China's performance in WWII. It was ugly, but respectable. Aside from the Flying Tigers (later the 14th air force), Allies support for China was minimal (relative to the support Russia received). Chiang had a premodern military, with an agrarian economy (having lost the most developed part of the country to Japan in the first years of the war). But the Chinese held the Japanese at bay for the entire War, tying down millions of japanese soldiers (inflicting millions of casualties), depriving Japan of resources that could have been directed towards the Pacific.

Ultimately, China was instrumental to the defeat of Japan. Had China surrendered like France. Chinese slave labor, Chinese mineral resources, Chinese grain, even impressed Chinese soldiers. along with hundreds of thousands of japanese troops would have been sent in the total war against the US.

That would have made the war in the Pacific at least an order of magnitude more difficult.

• "Ultimately, China was instrumental to the defeat of Japan."

My take: I'd go further, and say not just Japan, but also Germany.

On China's contribution to the Allies during WW2, which has been perenially & conveniently minimised as incompetent, here's the opinion of Hans van de Ven - a noted authority on 20th century China and the formation of the Chinese Communist Party - emphasis mine:

The time has come to disaggregate the Second World War and become attuned to the differences in each of its theatres. That is not to say that no connections existed between them: the Second World War was an alliance war, which the Allies won because they worked together much better than the Axis powers. Alliance members provided troops, ammunition and other aid to each other. America, a land of increasing plenty, supplied not just arms and ammunition but also food to Britain and the USSR. Events in one theatre impacted on others. The war in China made it difficult for Japan to join Germany’s war against the Soviet Union, leaving the latter free to concentrate on fighting the Wehrmacht. Had Japan succeeded in forcing a Chinese surrender, then China’s resources would have become available to Japan. We can only speculate about the consequences, but they would have been significant.

Source: China at War (Harvard, 2018), Introduction.

This will be an unpopular view, but I would suggest the biggest blunder is a failure to exploit Japan's peace offers prior to 1938. Remember that Imperial Japan was wracked with internal conflicts and factionalism, and that its establishment historically viewed the Soviet Union as its primary enemy. When the war in China broke out, significant voices in the civil government and military high command sought to keep the conflict limited.

The most well known part of their efforts is the Trautmann mediation. On 2 November 1937, Japan asked the German ambassador Trautmann to transmit some relatively lenient peace terms:

1. China to join the Anti-Comintern Pact
2. Break off relations with the Soviet Union
3. Put an end to the Chinese anti-Japan movement
4. Autonomy for Inner Monolia
5. Demilitarisation Zone on border with Manchukuo and in Shanghai

This initial offer was rejected immediately. At this stage, Japanese High Command had no plans to move on Nanking. On 7 November, the Army General Staff issued an order limiting operations in the theatre to a line east of Suzhou and Jiaxing. This order was subsequently disregarded by Japanese units on the ground on 19 November. The Japanese government then repeated its previous peace terms on 22 November.

This time Chiang held a high level meeting of the Chinese government, which concluded that, with no demand for reparations or recognition of Manchukuo, the terms were actually acceptable. Chinese acceptance was transmitted to Trauntmann on 2 December for relaying to Japan - by which point, Japanese forces were on the verge of capturing Nanking.

With the fall of Nanking, initiative within the Japanese government had passed completely into the hands of the hawks. The list of demands were amended to include an unspecified amount of reparations as well as a unified anti-communism front that now includes Manchukuo - that is to say, Japan now demanded Chinese recognition of Manchukuo.

These terms were considered beyond the pale by the Chinese government. With Japanese doves cowed and open talk of using the truce to rearm by Chinese notables, the peace effort fell apart.

The failure of the Trauntmann mediation led Germany to completely abandon China as an ally. Apart from economic/industrial aid, the more immediately important shipments of military supplies and arms were halted, and German military advisors were ordered to leave. Those were substantial losses China was ill equipped to replace herself - and in 1938, China needed every little scrap of anything it could possibly get.

On the other hand, although long lasting peace was unsustainable (probably), a temporary truce in 1937 would still have benefited China immensely. The German trained and equipped elite Chinese forces, freshly eviscerated on the bloody streets of Shanghai, would have had time to rebuild and expand. Chinese industrial expansion could have been undertaken, and relocating them to the interior would not have had to be achieved with massive sacrifices under enemy fire.

EDIT: A note on the political feasibility of a truce with Japan. While not exactly a populist strategy, it wasn't unacceptable to China at large either. I think this can be illustrated into two incidents where non-Chiang-aligned, regional cliques rebelled (purportedly to fight the Japanese): the Liangkwang Incident, and the rather more successful/famous Xi'an Incident.

The Liangkwang Incident began on June 1, 1936. The Guangdong and Guangxi cliques telegraphed a denouncement of Chiang's central government over "inaction" against Japanese imperialism. They then announced that their forces were moving into Hunan.

But by June 10 the central government's forces had blocked the cliques' armies, and Hunan's regional government sided with the Nationalist government. Not long thereafter, Cantonese generals led by Yu Han-Mou pledged loyalty to the central government and moved against their former comrades, who retreated without putting up a fight. Then the entirety of the Cantonese air force took off and defected, followed by the rest of the Guangdong clique's army.

The Guanxi clique fared rather more successfully, maintaining internal cohesion until September, when the Guanxi clique resubmitted to Chiang in exchange for the central government's agreement to cease encroaching upon their territory. But nonetheless the cliques, contrary to their anti-Japan slogans, were ultimately motivated by regional political interests. More to the point, the basis of Chiang's power was not much shaken by having to fight against an anti-Japan faction.

The Xi'an incident provides an indicator of contemporary public opinion. Not only did the central government continue to support Chiang after his capture during the "armed remonstrance", the mutineers were widely condemned in the court of public opinion.

On December 13, members of Nanking's universities including professor Lo Chia-Luen telegraphed their condemnations to Chang Hsueh Liang. The Peking and Shanghai universities (Mei I-chi, Chiang Monlin, Herman Liu) followed on December 14. The next day, over a hundred newspaper publishers published a joint declaration decrying the Fengtian Clique's actions. On December 16, more than two hundred magazines issued a similar condemnation. And on the same day the Tsing Hua University transmitted their denouncement of Chang's "rebellion", drafted by among others Wen I-To. The influential Ta Kung Pao published Hu Shih's "The Treason of Chang Hsueh Liang" on Dec 20, denouncing Chang and voicing support for maintaining peace to strengthen China.

Much of the intellectual elites of China (many of whom were themselves well acquainted with Japanese modernisation) recognised the lopsided military balance. Chang's actions in initiating the Xi'an Incident were widely lambasted as using the guise of resisting that Japanese to destroy national unity and strength. Chinese intellectuals at the time were inevitably aware of how the previous ethnic Chinese regime, the Ming Dynasty, fell to a war on two fronts - internal and external - against Manchuria. And the slogan of pacify the nation to resist foreigners has had a long tradition dating back to the Spring and Autumn period (as the term later borrowed into Japan as Sonnō Jōi).

Add in the fact that warlords were primarily concerned with their personal powers, then it would seem the biggest voice against compromise would be that of the common folk. I'm not sure that, in an impoverished China ruled by warlords, their voices carry much political weight.